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Angew Chem Int Ed Engl. 2015 Jan 12;54(3):734-44. doi: 10.1002/anie.201404856. Epub 2014 Nov 3.

Palladium-catalyzed anti-Markovnikov oxidation of terminal alkenes.

Author information

1
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen (The Netherlands).

Abstract

The palladium-catalyzed oxidation of alkenes, the Wacker-Tsuji reaction, is undoubtedly a classic in organic synthesis and provides reliable access to methyl ketones from terminal alkenes under mild reaction conditions. Methods that switch the selectivity of the reaction to provide the aldehyde product are desirable because of the access they provide to a valuable functional group, however such methods are elusive. Herein we survey both the methods which have been developed recently in achieving such selectivity and discuss common features and mechanistic insight which offers promise in achieving the goal of a general method for anti-Markovnikov-selective olefin oxidations.

KEYWORDS:

aldehydes; alkenes; palladium; reaction mechanisms; regioselectivity

PMID:
25367376
DOI:
10.1002/anie.201404856

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